51543-40-9

Basic information

• Product Name: (R)-2-Flurbiprofen
• Synonyms: (R)-2-Fluoro-α-methyl-1,1'-biphenyl-4-acetic acid;(R)-α-Methyl-2-fluoro-1,1'-biphenyl-4-acetic acid;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe;[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-Methyl-,(aR)-;Flurizan;MPC 7869;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid 97%;(R)-Flurbiprofen, >=99%
• CAS NO: 51543-40-9
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.26
• EINECS: 257-264-7
• Product Categories: API;Pharmaceutical ingredients
• Mol File: 51543-40-9.mol
• Article Data: 72

Chemical Properties

• Melting Point: 110-113 °C(lit.)
• Boiling Point: 376.2 °C at 760 mmHg
• Flash Point: 181.3 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.199 g/cm³
• Vapor Pressure: 2.84mmHg at 25°C
• Refractive Index: 1.34
• PKA: 4.14±0.10(Predicted)
• CAS DataBase Reference: (R)-2-Flurbiprofen(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Flurbiprofen(51543-40-9)
• EPA Substance Registry System: (R)-2-Flurbiprofen(51543-40-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 51543-40-9(Hazardous Substances Data)

Usage

Description

(R)-Flurbiprofen is a COX-inactive enantiomer of the racemic non-selective COX inhibitor flurbiprofen that has diverse biological activities. It inhibits γ-secretase activity in vitro and, in vivo, it reduces formation of amyloid-β peptide 1-42 (Aβ42) and improves axonal transport in young Aβ-plaque free mice but not old mice with existing Aβ plaques in the Tg2576 transgenic model of Alzheimer''s disease. (R)-Flurbiprofen inhibits NF-kB activation and DNA binding as well as AP-1 DNA binding in RAW 264.7 macrophages and reduces paw edema in a rat model of zymosan-induced inflammation via COX-independent inhibition of NF-κB and AP-1 activation when administered at doses of 1, 3, and 9 mg/kg. It also suppresses prostate tumor cell growth in vitro by inducing p75NTR protein expression and reduces tumor growth and metastasis in multiple mouse models of intestinal neoplasia.

Uses

(R)-2-Flurbiprofen is the R-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Biochem/physiol Actions

gamma secretase inhibitor; amyloid Abeta 42 lowering agent

InChI:InChI=1/C12H4F14/c13-7(9(15,16)17,10(18,19)20)5-1-2-6(4-3-5)8(14,11(21,22)23)12(24,25)26/h1-4H

Upstream product

• 5104-49-4 fluorobiprofen 
• 62784-66-1 bis(1-naphthyl)methanol 
• 185981-25-3 C₃₀H₂₄F₂O₃ 
• 64-17-5 ethanol 
• 42771-82-4 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid 
• 70312-66-2 benzyl 2-(2-fluoro-biphenyl-4-yl)propionate 
• 64858-90-8 ethyl 2-(2-fluoro-4-biphenylyl)-propionate 
• 56430-76-3 2-(2-fluoro-biphenyl-4-yl)-propionaldehyde 
• 168275-51-2 R-2-(3-fluoro-4-phenyl)phenylpropionaldehyde 
• 201230-82-2 carbon monoxide 
• 63444-55-3 4-ethenyl-2-fluorobiphenyl 
• 41604-19-7 1-bromo-3-fluoro-4-phenylbenzene 
• 64-18-6 formic acid 
• 136434-77-0 4-bromo-3-fluoroiodobenzene 

Downstream Products

• 5104-49-4 fluorobiprofen 
• 5104-49-4 (R)-flurbiprofen 
• 5104-49-4 (S)-(+)-flurbiprofen 
• 52807-12-2 2-(2-fluoro-4'-hydroxy-biphenyl-4-yl)-propionic acid 

Relevant articles and documents

An efficient method for the synthesis of (S)-flurbiprofen by 1,2-rearrangement of the aryl group

(S)-Flurbiprofen (1) is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve pain and inflammation associated with osteoarthritis. Herein a new and practical method for the preparation of 1 from 4-bromo-2-fluorobiphenyl (2) is reported, which achieves a good overall yield (20%) and high enantioselectivity (96%). This method avoids the use of expensive catalysts and affords the possibility of large-scale manufacturing with simple operations.

Deracemization through photochemical E/Z isomerization of enamines

Catalytic deracemization of a-branched aldehydes is a direct strategy to construct enantiopure a-tertiary carbonyls, which are essential to pharmaceutical applications. Here, we report a photochemical E/Z isomerization strategy for the deracemization of a-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic a-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochemical E/Z isomerization strategy for externally tuning enamine catalysis.

Synthesis of a TNF inhibitor, flurbiprofen and an: I -Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents

The copper-catalyzed substitution reaction of diethyl phosphate derived from TMSCCCH(OH)CH2CH2OTBDPS with 3-c-C5H9-4-MeOC6H3MgBr, followed by several transformations, afforded a tumor necrosis factor inhibitor possessing a Ph-acetylene moiety. The inhibitor was also synthesized from phenylacetylene phosphate PhCCCH(OP(O)(OEt)2)CH2CH2OTBDPS. Furthermore, the substitution of phosphates derived from TMSCCCH(OH)CH3 and TMSCCCH(OH)-i-Pr with 3-F-4-PhC6H3MgBr gave the corresponding substitution products, which were transformed to flurbiprofen and its i-Pr analogue, respectively. The copper-catalyzed substitutions in these syntheses proceeded in a regio- and stereoselective manner. This journal is